Bis{N-[2-hy-droxy-1,1-bis-(hy-droxy-methyl)eth-yl]glycinato-κ(3) O,N,O'}iron(II).

In the title compound, [Fe(C6H12NO5)2], the Fe(II) ion lies on an inversion center and is coordinated by two N atoms and four O atoms from two tridentate N-[2-hy-droxy-1,1-bis-(hy-droxy-methyl)eth-yl]glycine ligands, forming a slightly distorted octa-hedral coordination environment. In the crystal, O-H⋯O, O-H⋯N and weak C-H⋯O hydrogen bonds link mol-ecules, forming a three-dimensional network.

Related literature

For background to the applications of tripodal alcohols as single-mol­ecule magnets, see: Pilawa et al. (1998 ▶); Brechin (2005 ▶); Murugesu et al. (2005 ▶).

Experimental

Crystal data

[Fe(C6H12NO5)2]

M = 412.18

Monoclinic,

a = 8.8198 (7) Å

b = 9.0245 (7) Å

c = 12.3533 (7) Å

β = 127.224 (4)°

V = 782.94 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.02 mm−1

T = 298 K

0.19 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.829, T max = 0.923

4000 measured reflections

1708 independent reflections

1230 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.099

S = 1.04

1708 reflections

131 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681401397X/lh5715sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401397X/lh5715Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401397X/lh5715Isup3.cdx

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Fe(C6H12NO5)2]	F(000) = 432
Mr = 412.18	Dx = 1.748 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 621 reflections
a = 8.8198 (7) Å	θ = 2.9–21.9°
b = 9.0245 (7) Å	µ = 1.02 mm−1
c = 12.3533 (7) Å	T = 298 K
β = 127.224 (4)°	Sheet, colorless
V = 782.94 (10) Å3	0.19 × 0.16 × 0.08 mm
Z = 2

Bruker SMART CCD diffractometer	1708 independent reflections
Radiation source: fine-focus sealed tube	1230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
multi–scan	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.829, Tmax = 0.923	k = −11→11
4000 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3
1708 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.46 e Å−3
4 restraints	Δρmin = −0.39 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.5000	0.5000	0.01527 (19)
O1	−0.0265 (4)	0.7341 (3)	0.0516 (3)	0.0347 (7)
O2	0.0173 (4)	0.8369 (3)	0.3530 (3)	0.0355 (7)
O3	0.4719 (4)	0.7180 (3)	0.5354 (3)	0.0323 (7)
O4	0.6437 (4)	0.6393 (3)	0.2600 (3)	0.0356 (7)
O5	0.6619 (3)	0.5743 (3)	0.4408 (2)	0.0283 (6)
N1	0.2766 (4)	0.5686 (3)	0.2962 (3)	0.0209 (6)
C1	0.2121 (5)	0.7215 (4)	0.2983 (3)	0.0190 (8)
C2	0.3608 (5)	0.5508 (4)	0.2233 (3)	0.0237 (8)
H2A	0.2927	0.6132	0.1430	0.028*
H2B	0.3466	0.4488	0.1940	0.028*
C3	0.5700 (5)	0.5920 (4)	0.3128 (4)	0.0243 (8)
C4	0.1289 (5)	0.8101 (4)	0.1682 (4)	0.0276 (9)
H4A	0.0855	0.9056	0.1758	0.033*
H4B	0.2274	0.8276	0.1572	0.033*
C5	0.0626 (5)	0.6982 (4)	0.3222 (4)	0.0269 (8)
H5A	−0.0516	0.6556	0.2416	0.032*
H5B	0.1112	0.6298	0.3971	0.032*
C6	0.3822 (5)	0.8077 (4)	0.4165 (4)	0.0269 (8)
H6A	0.4712	0.8302	0.3973	0.032*
H6B	0.3396	0.9003	0.4299	0.032*
H1A	0.182 (4)	0.506 (3)	0.259 (3)	0.027 (10)*
H3A	0.514 (6)	0.773 (5)	0.605 (3)	0.078 (18)*
H1B	−0.126 (5)	0.787 (5)	0.014 (5)	0.10 (2)*
H2C	0.019 (7)	0.815 (5)	0.421 (4)	0.080 (19)*

	U11	U22	U33	U12	U13	U23
Fe1	0.0159 (4)	0.0181 (3)	0.0101 (4)	0.0003 (3)	0.0069 (3)	0.0009 (3)
O1	0.0265 (16)	0.0462 (18)	0.0188 (15)	0.0048 (14)	0.0070 (14)	0.0003 (13)
O2	0.0443 (18)	0.0349 (16)	0.0402 (19)	0.0148 (13)	0.0323 (16)	0.0086 (14)
O3	0.0379 (17)	0.0292 (15)	0.0160 (15)	0.0004 (13)	0.0091 (14)	−0.0017 (12)
O4	0.0293 (15)	0.0513 (18)	0.0283 (16)	0.0014 (13)	0.0185 (14)	0.0135 (13)
O5	0.0234 (14)	0.0396 (15)	0.0174 (14)	0.0003 (12)	0.0100 (12)	0.0048 (12)
N1	0.0203 (16)	0.0195 (16)	0.0220 (17)	−0.0026 (13)	0.0123 (15)	−0.0040 (13)
C1	0.0192 (18)	0.0201 (18)	0.0148 (19)	0.0020 (14)	0.0087 (16)	0.0019 (14)
C2	0.0213 (19)	0.0286 (19)	0.018 (2)	0.0028 (15)	0.0103 (17)	−0.0004 (15)
C3	0.026 (2)	0.0218 (19)	0.024 (2)	0.0015 (16)	0.0141 (18)	0.0035 (16)
C4	0.027 (2)	0.029 (2)	0.022 (2)	0.0025 (17)	0.0123 (19)	0.0029 (17)
C5	0.027 (2)	0.031 (2)	0.025 (2)	0.0050 (17)	0.0166 (19)	0.0038 (17)
C6	0.025 (2)	0.027 (2)	0.023 (2)	−0.0003 (16)	0.0121 (18)	−0.0005 (17)

Fe1—O3i	2.062 (3)	N1—C1	1.498 (4)
Fe1—O3	2.062 (3)	N1—H1A	0.871 (18)
Fe1—O5i	2.071 (2)	C1—C4	1.527 (4)
Fe1—O5	2.071 (2)	C1—C6	1.529 (5)
Fe1—N1	2.145 (3)	C1—C5	1.531 (4)
Fe1—N1i	2.145 (3)	C2—C3	1.515 (5)
O1—C4	1.427 (4)	C2—H2A	0.9700
O1—H1B	0.850 (19)	C2—H2B	0.9700
O2—C5	1.433 (4)	C4—H4A	0.9700
O2—H2C	0.854 (19)	C4—H4B	0.9700
O3—C6	1.426 (4)	C5—H5A	0.9700
O3—H3A	0.855 (19)	C5—H5B	0.9700
O4—C3	1.242 (4)	C6—H6A	0.9700
O5—C3	1.277 (4)	C6—H6B	0.9700
N1—C2	1.482 (4)
O3i—Fe1—O3	180.000 (1)	N1—C1—C5	104.9 (3)
O3i—Fe1—O5i	87.88 (10)	C4—C1—C5	110.7 (3)
O3—Fe1—O5i	92.12 (10)	C6—C1—C5	110.3 (3)
O3i—Fe1—O5	92.12 (10)	N1—C2—C3	111.5 (3)
O3—Fe1—O5	87.88 (10)	N1—C2—H2A	109.3
O5i—Fe1—O5	180.0	C3—C2—H2A	109.3
O3i—Fe1—N1	99.75 (10)	N1—C2—H2B	109.3
O3—Fe1—N1	80.25 (10)	C3—C2—H2B	109.3
O5i—Fe1—N1	99.68 (10)	H2A—C2—H2B	108.0
O5—Fe1—N1	80.32 (10)	O4—C3—O5	123.4 (3)
O3i—Fe1—N1i	80.25 (10)	O4—C3—C2	119.6 (3)
O3—Fe1—N1i	99.75 (10)	O5—C3—C2	117.0 (3)
O5i—Fe1—N1i	80.32 (10)	O1—C4—C1	111.5 (3)
O5—Fe1—N1i	99.68 (10)	O1—C4—H4A	109.3
N1—Fe1—N1i	180.000 (1)	C1—C4—H4A	109.3
C4—O1—H1B	109 (4)	O1—C4—H4B	109.3
C5—O2—H2C	102 (3)	C1—C4—H4B	109.3
C6—O3—Fe1	112.7 (2)	H4A—C4—H4B	108.0
C6—O3—H3A	109 (3)	O2—C5—C1	110.0 (3)
Fe1—O3—H3A	137 (3)	O2—C5—H5A	109.7
C3—O5—Fe1	114.9 (2)	C1—C5—H5A	109.7
C2—N1—C1	116.4 (3)	O2—C5—H5B	109.7
C2—N1—Fe1	103.9 (2)	C1—C5—H5B	109.7
C1—N1—Fe1	109.5 (2)	H5A—C5—H5B	108.2
C2—N1—H1A	106 (2)	O3—C6—C1	107.9 (3)
C1—N1—H1A	111 (2)	O3—C6—H6A	110.1
Fe1—N1—H1A	110 (2)	C1—C6—H6A	110.1
N1—C1—C4	114.2 (3)	O3—C6—H6B	110.1
N1—C1—C6	108.8 (3)	C1—C6—H6B	110.1
C4—C1—C6	107.9 (3)	H6A—C6—H6B	108.4
O5i—Fe1—O3—C6	−120.1 (2)	Fe1—N1—C1—C6	32.2 (3)
O5—Fe1—O3—C6	59.9 (2)	C2—N1—C1—C5	156.7 (3)
N1—Fe1—O3—C6	−20.6 (2)	Fe1—N1—C1—C5	−85.9 (3)
N1i—Fe1—O3—C6	159.4 (2)	C1—N1—C2—C3	83.5 (4)
O3i—Fe1—O5—C3	84.2 (2)	Fe1—N1—C2—C3	−37.0 (3)
O3—Fe1—O5—C3	−95.8 (2)	Fe1—O5—C3—O4	178.2 (3)
N1—Fe1—O5—C3	−15.3 (2)	Fe1—O5—C3—C2	−2.4 (4)
N1i—Fe1—O5—C3	164.7 (2)	N1—C2—C3—O4	−152.0 (3)
O3i—Fe1—N1—C2	−62.5 (2)	N1—C2—C3—O5	28.6 (4)
O3—Fe1—N1—C2	117.5 (2)	N1—C1—C4—O1	56.5 (4)
O5i—Fe1—N1—C2	−152.0 (2)	C6—C1—C4—O1	177.6 (3)
O5—Fe1—N1—C2	28.0 (2)	C5—C1—C4—O1	−61.6 (4)
O3i—Fe1—N1—C1	172.4 (2)	N1—C1—C5—O2	168.6 (3)
O3—Fe1—N1—C1	−7.6 (2)	C4—C1—C5—O2	−67.7 (4)
O5i—Fe1—N1—C1	82.9 (2)	C6—C1—C5—O2	51.6 (4)
O5—Fe1—N1—C1	−97.1 (2)	Fe1—O3—C6—C1	43.9 (3)
C2—N1—C1—C4	35.4 (4)	N1—C1—C6—O3	−49.6 (3)
Fe1—N1—C1—C4	152.8 (2)	C4—C1—C6—O3	−174.0 (3)
C2—N1—C1—C6	−85.3 (3)	C5—C1—C6—O3	65.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ii	0.87 (2)	2.10 (2)	2.952 (4)	166 (3)
O3—H3A···O4iii	0.86 (2)	1.72 (2)	2.562 (4)	167 (5)
O1—H1B···O5iv	0.85 (2)	1.96 (2)	2.804 (4)	174 (6)
O1—H1B···O4iv	0.85 (2)	2.59 (5)	3.172 (4)	127 (4)
O2—H2C···O1iii	0.85 (2)	1.93 (2)	2.779 (4)	170 (5)
C5—H5B···O5i	0.97	2.56	3.452 (4)	153
C2—H2A···O1	0.97	2.56	3.184 (4)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.87 (2)	2.10 (2)	2.952 (4)	166 (3)
O3—H3A⋯O4ii	0.86 (2)	1.72 (2)	2.562 (4)	167 (5)
O1—H1B⋯O5iii	0.85 (2)	1.96 (2)	2.804 (4)	174 (6)
O1—H1B⋯O4iii	0.85 (2)	2.59 (5)	3.172 (4)	127 (4)
O2—H2C⋯O1ii	0.85 (2)	1.93 (2)	2.779 (4)	170 (5)
C5—H5B⋯O5iv	0.97	2.56	3.452 (4)	153
C2—H2A⋯O1	0.97	2.56	3.184 (4)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .